Every agency has experienced this at least once: the proposal went out two weeks ago, and radio silence ever since.
Do you follow up again? Wait longer? Move on?
Jonathan Pritchard, CMO and previously the Senior Marketing Consultant at Thrive Internet Marketing Agency, describes the mental gymnastics perfectly.
He calls it "concerned grandma energy"—like when grandma wants to know you made it home safely, but you didn't call to tell her.
"So I'm still worried, even though I know you made it home," he explains. "That's why, even though I know they've seen it, they've looked at it, I'll say, 'Did it make it to you? I haven't heard from you."
The modern reality makes this even more awkward. Your proposal platform shows they've opened it 15 times, but you're still playing dumb and pretending you don't know they've read every word.
What if your follow-up system could see exactly how prospects engage with your proposal and respond accordingly?
We'll cover how to build intelligent automation that tracks engagement, reaches all decision makers, and eliminates the psychological games entirely.
Why your current follow-up process wastes time
Most follow-up with leads is busy work. You send proposals, wait, send 'checking in' emails, repeat. This burns hours without moving deals forward.
Let’s look at three ways manual follow-up processes drain time and energy.
They consume too much time
The math is simple but brutal: three active proposals with daily check-ins means 15 touchpoints per week. Scale that across a growing pipeline, and you're spending entire days just managing follow-up emails.
Damien Elsing, Founder of HubSpot Partner Consulting Agency CLCK, knows this tension well.
"Follow-ups are kept close together, ideally daily touchpoints, because the client usually has an urgent problem they want solved," he explains.
The logic makes sense—urgent problems need urgent attention. But when every prospect feels urgent, your team gets trapped in a cycle of constant check-ins that eat up bandwidth without necessarily moving deals forward.
The irony is that the more sales proposals you send (which should be good for business), the more unsustainable your follow-up workload becomes. Something has to give.
Too many stakeholders dilute your message
Your proposal doesn't live in a vacuum. Once you hit send, it enters a complex internal ecosystem where people you've never met interpret, summarize, and pass around your carefully crafted message.
Jonathan puts it perfectly:
"In enterprise, business-to-business, kind of sales, there are so many people involved in saying yes or no that you kind of present it and then put it in their hands, and then they've gotta go have a whole bunch of conversations with a whole bunch of people that you may never even talk to."
Your main contact becomes a game of telephone. They're advocating for your proposal to people who weren't part of your discovery calls and don't understand your approach. Key details get lost or misrepresented along the way.
The person responding to your follow-ups might love your approach but lack the authority to move forward.
You're playing information games without realizing it
The weirdest part about modern proposal follow-up is the charade everyone pretends to play. Your tracking dashboard shows they've opened the proposal 15 times across three different devices. They've spent 45 minutes reviewing section two. Yet your follow-up emails still start with "Just wanted to make sure you received this."
Jonathan nails the absurdity:
"Part of the follow-up is staying in touch with your person to hear the news secondhand about how it's going. So that's why a lot of times, having the tracking on how long somebody spent looking at the proposal is really important."
We have more data about prospect engagement than ever before, but we're still following scripts from the PDF era. Meanwhile, your contact filters information back to you based on what they're comfortable sharing. Everyone has incomplete information but pretends they don't.
This creates unnecessary friction in straightforward conversations.
Three layers to automate your follow-up process
Instead of treating follow-up as a series of manual check-ins, think of it as three interconnected systems that work together. Each layer builds on the previous one, creating a comprehensive proposal automation framework that handles everything from initial proposal delivery to final stakeholder coordination.
When all three layers are working in sync, you eliminate the guesswork and create predictable touchpoints that feel personal without requiring constant manual intervention.
Layer 1: Fix how you deliver proposals
Present your proposal live
The biggest mistake agencies make is treating proposals like documents instead of conversations. Emailing a PDF and hoping for the best turns your strategy into homework nobody wants to do.
Damien's approach changes the entire dynamic:
"Ideally, we don't just send a proposal; we aim to present it during a call with the client. The goal is to get verbal sign-off on the call, making the e-signing a formality."
When you walk through your proposal live, you can address objections in real-time, emphasize key points, and gauge reactions immediately. Questions that might derail a deal via email become collaborative discussions that move things forward.
Automate the logistics with calendar scheduling tools that include pre-call questionnaires. Build template scripts that guide the conversation while leaving room for natural dialogue.
For example:
Opening (2 minutes) | "Thanks for joining today. I know you've had a chance to review the proposal, so rather than reading through everything, I want to walk through the key strategic pieces and make sure we're aligned on approach and timeline. Sound good?" |
Strategy Overview (5 minutes) | "Let's start with the core challenge we discussed—[specific problem]. Our approach tackles this through three phases: [brief overview]. The reason we structured it this way is [rationale]. Does this align with how you're thinking about solving this?" |
Investment Discussion (3 minutes) | "Looking at the investment, we've broken this into [payment structure]. This reflects the value delivery timeline we discussed, where you'll see [specific outcomes] by [timeframe]. Any questions on how we've structured this?" |
Timeline & Next Steps (2 minutes) | "If we move forward, we'd start [date] with [first deliverable]. The key milestone dates are [list]. What does your internal approval process look like from here?" |
Close for Commitment | "Based on what we've covered, do you feel confident this approach will solve [their problem]? What questions do you have before we move to next steps?" |
Make live presentations as routine as sending emails, but infinitely more effective at closing deals.
Make signing effortless with the right technology
PDFs create friction at the worst possible moment. Prospects have to download, print, sign, scan, and email back—or figure out digital signature software they've never used. Interactive proposals eliminate these steps with embedded signing capabilities.
William Maxwell Le Normand, Founder of Webflow production agency, Ish.Studio, saw this firsthand:
"It's a lot easier to sign the deal when we send out proposals with Qwilr. Before we sent out a PDF that the client needed to figure out how to sign. We did not make it easy for them before…But now we have about 28-33% closing rate on outbound sales."
E-signature software like Qwilr lets prospects approve and sign contracts directly within the proposal—no downloads, no printing, no separate software required.
The entire process happens in one seamless experience that removes every possible point of friction between "yes" and "signed."
Layer 2: Respond based on what prospects actually do
Stop pretending you don't know they've seen it
The polite fiction of proposal follow-up is exhausting for everyone involved.
Jonathan reiterates,
"I know where you are. I know that you've gotten the proposal. I know you've looked at it 15 times in the past three days, but you haven't told me that you have. You didn't tell me that you got it. So I'm operating under the context of how much information you've given me, which was zero."
The data available today makes this charade even more ridiculous. Platforms like Qwilr provide section-by-section analytics that show exactly which parts prospects spend the most time reviewing.
You can see they've spent 20 minutes on your pricing section but skipped the case studies entirely.
Yet you're still pretending you don't know anything about their engagement.
But you can acknowledge this reality while still maintaining professional courtesy.
Jonathan’s systematic approach:
"Even though I know they've seen it, they've looked at it, I'll say, Did it make it to you? I haven't heard from you. So I just want to make sure that this is too important for your business to not keep on track."
This creates automated sequences that mirror natural human psychology:
- Day 1: "Making sure this got to you" (even when you know they opened it)
- Day 3: "Checking if you need clarification on anything"
- Week 1: "Following up on timeline discussions"
The key is building concern and urgency without breaking the social contract of pretending you don't have surveillance-level data on their reading habits.
Track engagement, then respond accordingly
Raw engagement data becomes powerful when you build automated responses around it. Send different follow-ups based on how people actually engage.
- High engagement signals (multiple views, long session times) trigger priority follow-up. These prospects are actively evaluating your proposal, so call them while they're engaged. Your automation should escalate these leads to personal outreach or schedule immediate calls while the momentum is high.
- No engagement after several days activates re-engagement sequences. Maybe your proposal got buried in their inbox, or the timing shifted. These automated touchpoints focus on resurfacing the proposal with different angles—urgency, social proof, or simplified next steps.
- Partial engagement (opening but not spending much time) suggests confusion or misalignment. These prospects get clarification-focused follow-ups: "I noticed you had a chance to review the proposal briefly. What questions can I answer to help you evaluate this properly?"
Qwilr’s detailed engagement analytics that show exactly how prospects interact with your proposals—time spent on each section, which devices they're using, and when they're most active.
This granular data lets you create follow-ups that acknowledge their specific interests and concerns rather than sending generic check-ins.
The beauty of behavior-triggered automation is that it feels personal because it responds to what prospects actually do, not arbitrary calendar dates.
Build systems to identify all decision makers
Your main contact is rarely the only person involved in the decision. The challenge is mapping the full buying committee without making your contact feel like you're going around them.
Here’s how to fix that:
- Start with automated stakeholder identification questionnaires built into your discovery process. Questions like "Who else will be evaluating this proposal?" and "What departments need to sign off on this investment?" surface the full decision-making landscape upfront.
- Create templates that make it easy for your contact to forward proposals to additional stakeholders. Include a brief summary email they can customize: "Here's the proposal we discussed. The key points relevant to your role are..." This reduces the burden on your champion while ensuring your message reaches everyone who matters.
- Different stakeholder types need different follow-up sequences. Technical stakeholders care about implementation details and integration. Financial stakeholders focus on ROI and budget impact. Executive stakeholders want strategic outcomes and risk mitigation.
Automation increases the likelihood that your proposal resonates with the specific concerns and priorities of each decision maker.
Coordinate touches across the buying committee
Once you know who's involved in the decision, your system should help you stay in touch with everyone without overwhelming your main contact. Set up automatic reminders to ask your contact to share specific parts with their team—like "Can you send the budget section to your finance person?"
Your follow-up system should send each person the information that matters to them, at the right time, without creating confusion or mixed messages. Everyone gets what they need to make a good decision.
How to automate content creation and follow-up messages
Let AI handle repetitive customization work
The biggest time sink in proposal creation isn't the strategy—it's adapting that strategy for each client. AI changes this completely by handling the repetitive customization while you focus on the high-level thinking.
As Damien explains,
"Now, with AI, we still don't spend a lot of time, but the output is much more customized. We input proposal examples, templates, client transcripts, and notes, and AI generates a well-structured, customized proposal."
William takes this further: "I would automate note-taking from meetings, then send that note to our AI knowledge base, which could customize the offer based on what we do, our resources, and so on."
Qwilr's AI Proposal Creator generates complete interactive proposals based on your business URL and simple prompts.
You describe your client and project in a few sentences, and the AI creates a structured proposal framework with relevant sections, case studies, and content suggestions tailored to that specific situation.
This approach becomes even more powerful with Qwilr's template libraries. You can set up proposals that automatically pull in the right case studies based on the client's industry and fill in ROI calculators with their specific numbers from discovery calls.
Automate content follow-ups
Follow-up questions often need more explanation than a quick email can provide.
Jonathan discovered this creates a content opportunity:
"Any further emailed questions that they send, I'll do a loom explanation of the answer, because often a very short question needs a real long explanation, and if you put all that into an email, they'll open it, see a novel's worth, and go, I'm not reading that, but they would watch a three minute video of you explaining it."
The genius is in shareability. Videos travel better internally than email chains because your contact can forward a clear, complete explanation instead of trying to summarize your written response.
Qwilr offers workflow automations that trigger based on proposal activity.
From sending notifications when prospects view specific sections to updating your CRM when deals close, you can eliminate countless manual tasks throughout the sales process.
Build educational drip sequences that share relevant case studies, industry insights, and problem/solution content over time. Instead of one-off responses, you're nurturing prospects with valuable content that keeps your expertise top of mind throughout their decision process.
How to maintain the human touch
Some situations will always need a human touch. The trick is building systems that identify these moments early and give you the context to handle them well.
- High-value deals requiring personal attention: Six-figure contracts need relationship-building that only humans can provide. Automation handles the logistics while you focus on strategic conversations that close deals.
- Complex stakeholder situations: Multithreaded sales with multiple decision makers who have conflicting priorities require personal navigation. Automated systems can identify the complexity, but human judgment determines how to address competing interests.
- Sensitive timing or political considerations: Layoffs, acquisitions, or leadership changes require careful messaging that adapts in real-time. Your automation flags these situations so you can intervene with appropriate tone and timing.
- Automated scheduling for human touchpoints: Let technology handle calendar coordination and prep work. Your CRM triggers personal outreach opportunities based on sales engagement patterns or deal stage milestones.
- AI-suggested talking points for personal calls: Pre-call briefings include recent proposal activity, stakeholder concerns, and conversation starters. You show up prepared without spending hours researching.
Let Qwilr handle the concerned grandma energy
Your biggest follow-up wins come from removing small friction points, not grand gestures. Qwilr quietly handles proposal delivery confirmations, tracks which sections prospects actually read, and sends you alerts when someone's ready for a call.
These micro-automations free up hours each week that you can redirect toward discovery calls and relationship building.
Ready to see how this works in practice? Start a free trial to explore Qwilr's automation features and discover which tools will have the biggest impact on your current follow-up process.
About the author
Kiran Shahid|Content Marketing Strategist
Kiran is a content marketing strategist with over nine years of experience creating research-driven content for B2B SaaS companies like HubSpot, Sprout Social, and Zapier. Her expertise in SEO, in-depth research, and data analysis allow her to create thought leadership for topics like AI, sales, productivity, content marketing, and ecommerce. When not writing, you can find her trying new foods and booking her next travel adventure."
